Réaction #2288379

Équation de réaction

1,3-Dimethyl-2,4-dioxo-5-phenyl-2,3,4,7-tetrahydro-1H-pyrimido[4,5-a]pyrrolizin-9-yl trifluoromethanesulfonate

lithium bromide

tributyl(5-methylfuran-2-yl)stannane

→

title product

1,3-Dimethyl-9-(5-methylfuran-2-yl)-5-phenyl-1H-pyrimido[4,5-a]pyrrolizine-2,4(3H,7H)-dione

Solvants

Et2O

THF

Conditions de réaction

Traitement

1. 1
   Températureto reflux for 10 mins
2. 2
   FiltrationThe reaction mixture was filtered through a glass
3. 3
   Filtrationfilter paper
4. 4
   Concentrationthe filtrate concentrated in vacuo
5. 5
   workup.DISSOLUTIONThe crude product was dissolved in the minimum amount DCM/EtOAc
6. 6
   Lavageeluted with 0-80% EtOAc in iso-hexane
7. 7
   LavageThe desired product was eluted at 30% EtOAc
8. 8
   Concentrationconcentrated
9. 9
   Autreto yield a yellow solid
10. 10
    Filtrationthe solid filtered

Mode opératoire

1,3-Dimethyl-2,4-dioxo-5-phenyl-2,3,4,7-tetrahydro-1H-pyrimido[4,5-a]pyrrolizin-9-yl trifluoromethanesulfonate (step 4) (100 mg, 0.227 mmol), Cul (4.31 mg, 0.023 mmol), lithium bromide (39.4 mg, 0.453 mmol), tributyl(5-methylfuran-2-yl)stannane (168 mg, 0.453 mmol) in THF (2 ml) and Pd-118 (14.77 mg, 0.023 mmol) were heated to reflux for 10 mins. The reaction mixture was filtered through a glass filter paper and the filtrate concentrated in vacuo. The crude product was dissolved in the minimum amount DCM/EtOAc and loaded onto a 12 g silica cartridge and eluted with 0-80% EtOAc in iso-hexane. The desired product was eluted at 30% EtOAc. The relevant fractions were combined and concentrated to yield a yellow solid. The isolated solid was suspended in Et2O and the solid filtered to yield the title product.

Source